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Henry VIII’s Love Letters and What They Tell Us About Anne Boleyn

Author guest post from Helene Harrison.

The set of seventeen love letters now in the Vatican are probably some of the best-known contemporary works we have relating to Anne Boleyn, though not one of them is written by her. Henry VIII notoriously hated writing yet penned a minimum of seventeen letters in his own hand in both English and French to the woman who would become his second wife – Anne Boleyn. But what can we learn about Anne through the king’s eyes?

Anne Boleyn, late 16th century, at the National Portrait Gallery (Photo is Author’s Own)

Anne Boleyn’s power over the king in the late 1520s lay in her role as the king’s emotional mistress. He confided in her, I think in a way he didn’t with anyone else – not Katherine of Aragon or any future wife, not any of the Thomases, Wolsey or Cromwell or More. His passion and obsession with Anne Boleyn is evidenced in the series of love letters, though we can only infer Anne’s responses from what Henry says, which leaves a lot open to interpretation.

The letters themselves aren’t dated, so it’s difficult to know exactly when to place them and in which order. Some historians place the earliest letters in 1528, others say 1526, and some even suggest as early as 1524. Given that we can’t be sure exactly when Henry VIII fell in love with Anne Boleyn and began his pursuit of her, the debate rages on.

One letter, which seems to be early in the sequence, says that Henry had ‘been for the whole year stricken with the dart of love’ and was keen to establish whether Anne felt the same way for him. Henry talks about how much he wants to see Anne, misses her when she’s away from court staying at Hever Castle, that ‘absence from you grieves me sorely’. Henry also sent Anne gifts, including a buck he killed with his own hand.

Henry VIII c.1520, at the National Portrait Gallery (Photo is Author’s Own)

We also have evidence of a gift that Anne Boleyn sent to Henry VIII, as the king describes it in a letter written to her:

For a present so beautiful that nothing could be more so (considering the whole of it), I thank you most cordially, not only on account of the fine diamond and the ship in which the solitary damsel is tossed about, but chiefly for the fine interpretation and the too humble submission which your goodness hath used towards me in this case.’

This gift is often taken as Anne submitting to Henry VIII and accepting his proposal of marriage. The ship was said to represent protection, like the ark that protected Noah in the Bible, and the diamond to represent constancy and devotion.

Another thing which appears across the letters, particularly in ones believed to be later in the sequence, is a sense of a physical relationship between Henry VIII and Anne Boleyn. Even if they weren’t having full intercourse, it seems Anne did allow Henry some access to her body. In one letter, Henry talks about how he wished himself ‘(especially in the evening) in my sweetheart’s arms, who pretty dukkys I trust shortly to cusse’. The fact that he writes about kissing her breasts tells us that there was some kind of a physical relationship, though how far it went and at what point in the relationship is unclear.

Other letters can be placed at the time of the sweating sickness outbreak in summer 1528. Anne Boleyn, her father, and her brother all fell ill, but survived. Henry received ‘afflicting news’ of ‘the illness of my mistress, whom I esteem more than all the world, and whose health I desire as I do my own, so that I would gladly bear half your illness to make you well’. This was quite a gesture on Henry’s part given his fear of any kind of illness or sickness.

Hever Castle, childhood home of Anne Boleyn where she likely received the king’s letters (Photo is Author’s Own)

What we do learn from the love letters Henry VIII sent to Anne Boleyn is the depth of his love for, and even obsession with, her. It is a feeling which is unmatched in any of his other romantic relationships in his life. Their relationship was one of sunshine and storms with angry arguments and passionate reconciliations. This tempestuous relationship no doubt led to Anne’s execution just three years into their marriage, along with her failure to produce a son and heir. But these love letters stand as testament to the great passion of Henry VIII’s life and offer a glimpse into Anne Boleyn and how she was perceived as she was just stepping onto the international stage.

If you want to read the series of love letters, Elizabeth Norton has published a brilliant collection of documents relating to Anne Boleyn including the love letters1, and the Vatican has digitised the original letters so you can view them online.2

You can buy my new book ‘The Many Faces of Anne Boleyn: Interpreting Image and Perception’ right now here.

1 Elizabeth Norton, Anne Boleyn: In Her Own Words and the Words of Those Who Knew Her (2011).

2 Vatican Archives, ref. Vat.lat.3731.pt.A, https://digi.vatlib.it/view/MSS_Vat.lat.3731.pt.A.